Skeletal isomerization of unsaturated fatty acids on Beta zeolites: Effects of calcination temperature and additives

Ha, Long; Mao, Jingbo; Zhou, Jingya; Zhang, Z. Conrad; Zhang, Shuguang

doi:10.1016/j.apcata.2008.12.018

Cited by 30 publications

(27 citation statements)

References 8 publications

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“…Most of the results from this work show conversion to branch chain products to be in the 30-40% range. This is consistent with the results of Ha et al [19], and Tolvanen et al [20], who have reported conversions of 32 and 30% branch chain isomers, respectively, using a zeolite based catalyst and oleic acid and linoleic acid as a starting material.…”

Section: Oleic Acid Studysupporting

confidence: 93%

Optimizing Reaction Conditions for the Isomerization of Fatty Acids and Fatty Acid Methyl Esters to Their Branch Chain Products

Reaume

Ellis

2010

J Americ Oil Chem Soc

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In order to improve the oxidative stability and cold flow properties of oleic acid or methyl oleate, branch chain isomerization was conducted using a beta zeolite catalyst. Reaction conditions of temperature (200-300°C), pressure (0.1-3.0 MPa), and co-catalyst (0-2 wt%) were optimized based on branch chain conversion and the cloud point of the ester following the isomerization reaction of oleic acid or methyl oleate. Fourier transform infrared spectroscopy (FTIR) and Gas Chromatograph equipped with Mass Spectrometry (GC/MS) analyses were used to analyze and quantify the isomerization product samples, while the cloud point of each sample was tested. The lowest and therefore, best cloud point measured was -15.2°C at conditions of 200°C, 3 MPa, and 2% co-catalyst using methyl oleate as a starting material. The highest branch chain conversion achieved was 50% under conditions of 300°C, 1.5 MPa and 0% co-catalyst using oleic acid as a starting material. The use of oleic acid and methyl oleate is based on whether it is optimal to carry out the skeletal isomerization before or after the esterification reaction. Performing the isomerization reaction on the ester was preferred over the fatty acid based on the trans isomerization and cloud point results. Reducing the unbranched trans isomers was desirable in obtaining a low cloud point. Keywords Fatty acid methyl ester Á Isomerization Á Branch chain Á FTIR Á Cloud point List of symbols MO Methyl oleate OA Oleic acid CP Cloud point BC Branch chain FTIR Fourier transform infrared spectroscopy FFA Free fatty acid(s) FAME Fatty acid methyl ester(s) GC/MS Gas chromatograph/mass spectrometry

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Section: Oleic Acid Studysupporting

confidence: 93%

Optimizing Reaction Conditions for the Isomerization of Fatty Acids and Fatty Acid Methyl Esters to Their Branch Chain Products

Reaume

Ellis

2010

J Americ Oil Chem Soc

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“…For instance, the product selectivity of bc‐FA is increased by 2, 2.5, and 10.6% with Ferrierite (entries 4 and 8, Table ), ZSM‐5 (entries 4 and 5, Table ), and BETA (entries 6 and 7, Table ) zeolites respectively due to the presence of water in the reaction. This specific activity is due to the formation of new Brønsted acid sites in the presence of water and/or by the mitigation of harmful effects of the carboxylic group on the acid sites of the zeolite . Along with these results, it is also noticed that the presence of water promotes the formation of lactones (BL + LL).…”

Section: Resultsmentioning

confidence: 68%

“…Several clays are used as catalysts in the acid dimerization process, where the yield of dimer/trimer acids and branched fatty acid are 75% and below 20%, respectively . More recently, large‐pore zeolites such as faujasite and Beta structure (pore size >6 Å) and mesoporous zeolites (>15 Å) have been used for skeletal isomerization of ulc‐FA with better yield of bc‐FA. Some other synthetic methodologies have also been reported to introduce alkyl branches in fatty acid chains such as thermally initiated addition of alkanes to unsaturated fatty acids, three step synthesis of iso‐fatty acid through the addition of methylmagnesium bromide, Lewis acid induced hydroalkylation or co‐oligomerization of fatty acids .…”

Section: Introductionmentioning

confidence: 99%

Convenient and Environmentally Friendly Production of Isostearic Acid with Protonic Forms of Ammonium Cationic Zeolites

Sarker

Latona

Moreau

et al. 2017

Euro J Lipid Sci & Tech

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Three ammonium‐cationic zeolites (ferrierite, ZSM5, and zeolite BETA) are individually analyzed to produce branched‐chain fatty acid (i.e., isostearic acid) from unsaturated linear‐chain fatty acid (ulc‐FA) with up to 98% conversion and 80% selectivity. The SiO2/Al2O3 molar ratio of zeolite, amount of water and choice of additive are found to be the key factors for the efficiency of zeolites in this particular reaction. Detailed characterization of zeolites supports the optimization parameters to produce the best results. Large scale production of isostearic acid achieving a 76% selectivity and 96% conversion demonstrates the potential of this system's capability at the pilot scale. Variation in isomeric composition of branched‐chain fatty acid (bc‐FA) product is observed for the three different catalytic methods. Dimer production due to interaction with the external acidic surface of these zeolites has been observed, but it can be suppressed. Practical Application: Lubricant, cosmetic and surfactant fields are examples where these biodegradable isostearic acid and other bc‐FA materials are applied. Three ammonium cationic zeolites (i.e., ferrierite, BETA, ZSM‐5) are used to produce the iso‐oleic acid (precursor of isostearic acid) with high selectivity. The iso‐oleic acid products are found to have different isomeric compositions which could potentially expand the application of the isostearic acid.

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“…Also two critical factors namely oxidation stability and cold flow properties (cloud point, pour/melting points and viscosity) need to be addressed when fatty acids are used directly or to make derivatives. Saturated fatty chains are stable whereas unsaturated fatty chains are prone to oxidation in air [193].…”

Section: Catalytic Applications Of Meso Porous Metal Oxidesmentioning

confidence: 99%

“…However, high catalyst loading and coke formation are still some problems that need to be addressed. Promising results were reported on the conversion of unsaturated fatty acid to branched isomers using modified Ferrierite [193,197,198],…”

Section: Catalytic Applications Of Meso Porous Metal Oxidesmentioning

confidence: 99%

Rational design of mesoporous gallium oxide and gallium-based mixed oxide catalysts.

Deshmane¹

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I would first like to express my gratefulness to my supervisor, Professor Moises A Carreon, who has guided me throughout my graduate work. I appreciate his advice, his professional comments and guidance, which have always enlightened me and I really appreciate his patience in reading my manuscript countless times. I would also like to acknowledge Dr. Paul Ratnasamy who has been a co-advisor to me and for providing a new direction to our work.

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Skeletal isomerization of unsaturated fatty acids on Beta zeolites: Effects of calcination temperature and additives

Cited by 30 publications

References 8 publications

Optimizing Reaction Conditions for the Isomerization of Fatty Acids and Fatty Acid Methyl Esters to Their Branch Chain Products

Optimizing Reaction Conditions for the Isomerization of Fatty Acids and Fatty Acid Methyl Esters to Their Branch Chain Products

Convenient and Environmentally Friendly Production of Isostearic Acid with Protonic Forms of Ammonium Cationic Zeolites

Rational design of mesoporous gallium oxide and gallium-based mixed oxide catalysts.

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